4-Methylmorpholine → HCID 20825553, compound

HRID 586131Notes

Reaction equation

HRID 586131 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:13][C:14]([CH3:17])([CH3:16])[CH3:15])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN1CCOCC1.ClC(OCC(C)C)=O.[NH2:33][C:34]1([C:39]#[N:40])[CH2:38][CH2:37][CH2:36][CH2:35]1>C1COCC1.O>[C:1]([O:5][C:6](=[O:7])[NH:8][CH:9]([C:10](=[O:12])[NH:33][C:34]1([C:39]#[N:40])[CH2:38][CH2:37][CH2:36][CH2:35]1)[CH2:13][C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 21068971-AminocyclopentanecarbonitrileHCID 47124962-(((Tert-butoxy)carbonyl)amino)-4,4-dimethylpentanoic acid

Product 1

HCID 20825553HCID 20825553, compoundYield 89.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 2-tert-butoxycarbonylamino-4,4-dimethyl-pentanoic acid (5 g, 20.3 mmol) and N-methyl morpholine (4.46 mL, 40.6 mmol) in THF (40 mL) at 0° C. was added isobutyl chloroformate (2.64 mL, 20.3 mmol) and, after 10 min, the solution of 1-amino-cyclopentanecarbonitrile (3.35 g, 30.5 mmol) in THF (40 mL). The mixture was allowed to warm to room temperature and stirred overnight. It was diluted with water, extracted with dichloromethane, washed with brine, dried (sodium sulfate) and concentrated to give the crude product. Chromatography on silica gel (dichloromethane:MeOH=30:1) gave [1-(1-cyano-cyclopentylcarbamoyl)-3,3-dimethyl-butyl]-carbamic acid tert-butyl ester (6.15 g, 89.6%).

Workup

  1. extractionextracted with dichloromethane
  2. washwashed with brine
  3. dry with materialdried (sodium sulfate)
  4. concentrationconcentrated
  5. customto give the crude product

Sources & evidence

ORD record
ord-aaf86a5ed12f444da78f034b66e08dbf
Source dataset
uspto-grants-2005_08
Patent number
US06936606B2

Reaction notes

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